VDG Camphor

STRUCTURE ELUCIDATION
OF CAMPHOR
Dr. V. D. Gulkari
Associate Professor
Priyadarshini J. L. College of Pharmacy Nagpur
•UV-VIS Spectrophotometer
•Infrared Spectrophotometer IR
•Nuclear Magnetic resonance NMR
•Mass Spectrophotometer MS
And various General Reaction & Molecular Refraction
Such as
Oxidation,
Reduction,
Brominating,
Iodination etc…..
i) Acyclic Terpenoids : They contain open structure.
ii) Monocyclic Terpenoids: They contain one ring in the structure.
iii) Bicyclic Terpenoids : They contain two rings in the structure.
iv) Tricyclic Terpenoids : They contain three rings in the structure.
v) Tetracyclic Terpenoids : They contain four rings in the structure
Relation between general formula of compound and type of compounds:
General formula of parent saturated Hydrocarbon Type of structure

CnH2n+2 Acyclic
CnH2n Monocyclic
CnH2n-2 Bicyclic
CnH2n-4 Tricyclic
CnH2n-6 Tetrayclic
Molecular formula: molecular formula is determined by usual quantitative analysis

and mol. wt determination methods and by means of mass spectrometry. If
terpenoid is optically active, its specific rotation can be measured.
CAMPHOR
Cinnamomum camphora Lauraceae
Solid ketone Obt. by steam distillation of
wood, leaves, roots or bark of camphor
tree. (camphor-oil+ camphor)sublimes at
room temp.
Camphor is a waxy, white or transparent

solid with a strong, aromatic odor. It is a
terpenoid with the chemical formula
C H O.
• optically active; (+) & (-). solid having
M.P. 180oC.
• It is used in pharmaceutical preparation
because of its analgesic, stimulant for heart
muscles, expectorant and antiseptic properties
in manufacture of celluloid, smokeless powder
and explosives, as moth repellent.
Industrially obtained from α pinene i.e. turpentine oil.
• α pinene Bornyl chloride Camphene
Isobornyl acetate Isoborneol Camphor

Biosynthesis of camphor
• GPP to LPP,
• LPP- Bornyl Pyrophosphate
• Bornyl Pyrophosphate-Borneol
• Borneol to camphor
REACTIONS
Saturated or unsaturated Nature???
• Camphor forms substitution product like
monobromocamphor,
• monochlorocamphor,
• camphor-sulphonic acid.
•
• The formation of these product shows that

camphor is a saturated compound.
Nature of Oxygen atom present
Nature of Oxygen atom present
• Nature of Oxygen atom in camphor is found to be
ketonic as it forms oxime with hydroxyl amine,
and phenyl hydrozone with phenyl hydrazine.
•
• C10H16O +H2NOH → C10H16=N-OH
• Camphor hydroxyl amine Oxime
• C10H16O + 2HN.NHC6H5 → C10H16=N-NH- C6H5

Camphor Phenyl hydrazine Phenyl hydrazone
Presence of- CO-CH2- group
Presence of -CO-CH2- group in camphor is
confirmed by its formation to iso-nitroso
derivative with amyl nitrite HONO &
monobenzylidene derivatives when
reacts with benzaldehyde Camphor
• The iso-nitroso derivatives is further hydrolysis
to yields camphor Quinone confirms the
presence of -CO-CH2- group in camphor.
• Camphor on reaction with benzaldehyde gives

monobenzylidene derivatives this reaction is
characteristic of reactive methylene group
attached to a KETONE -CO- , This shows that
camphor must contains -CO-CH2- group
Presence of 6membered ring,
ketonic Group, phenolic group
• Camphor is distilled with zinc chloride/P 2O5, forms P-
cymene. It is distilled with Iodine to form carvacrol.
This shows presence of one six member ring in
camphor. The presence of phenolic group in
carvacrol suggests the presence of ketonic group in
camphor
The formation of p-cymene reveals the presence of

6membered ring with one methyl and gem dimethyl groups
in camphor. It was reconfirm when camphor is heated with
hydroiodic acid HI, it yields tetra and hexa hydro m-xylene,
confirms a 6 membered ring.
Camphor on reaction with I2 gives carvacrol indicates the
presence of ketonic group that oxygenated to alcohol.
• Oxidation of camphor with HNO3 produces
camphoric acid & camphoronic acid.
• C10H16O C10H16O4 C9H14O6
• camphor Camphoric acid Camphoronic acid
• (3-O) (-1C, -2H, 5O)
• So by Knowing the structure of Camphoric acid

and Camphoronic acid separately and then to
get the final structure of camphor
Structure of Camphoronic acid
• Molecular formula C9H14O6
• It is saturated tricarboxylic acid,
• C9H14O6 It can be written as C6H11(COOH)3
• Its hydrocarbon C6H14 corresponds to CnH(2n+2)
• i.e. acyclic.
• Since camphoric acid is not easily decarboxylated,
its 3 carboxyl groups are attached to 3 different
carbon
• The exact structure is established; By
distillation under atmospheric-pressure gives,
isobutyric acid trimethyl succinic acid & CO2.
• The Bredt structure of camphoronic acid is proved
by its synthesis Perkin Junior and Thorpe in 1897
Halide
Aceto acetate Di methyl derivatives

ester
β Hydroxy acid
Structure of camphoric acid
• Molecular formula of camphoric acid is C10H16O4.
• It is found to be saturated dicarboxylic acid.
• Since its oxidised product camphoronic acid has a
GEM Di-methyl group and a separated Methyl
group, camphoric acid and camphor also must have
3 methyl group. Thus now the formula for
camphoric acid may be written as Me3C5H5(COOH)2
which leads C5H10 and its saturated parent HC with
Mol. For- C5H10 ==CnH2n=Monocyclic
• camphoric acid is a cyclopentane Dicarboxylic acid
• It forms monoester very easily but di-ester
with difficulty indicating two dissimilar
carboxyl group.
• It is found to be ring substituted glutaric acid
on the basis of Blanc rule.
• Glutaric acid Camphoric acid

• Finally structure of camphoronic acid & camphoric acid is established by synthesis
•UV-VIS Spectrophotometer
•Infrared Spectrophotometer IR
•Nuclear Magnetic resonance NMR
•Mass Spectrophotometer MS
•C10H16O=152
•CH3, C=O 15+12+16=43
•CH2=14
•152-137=15
Structure of Camphor :
• Structure of Camphor Molecular formula C10H16O, &
the general reactions & molecular refraction of
camphor show that it is saturated. The functional
nature of the oxygen atom was shown to be oxo as
camphor formed an oxime. It was a keto group since
camphor gives a dicarboxylic acid containing 10
carbon.
• From the foregoing facts it can be seen that the
parent hydrocarbon of camphor has the molecular
formula C10H18 ;this corresponds to CnH2n-2
• Structure confirmed by synthesis by (Haller1896) :
• Structure confirmed by synthesis by (Haller1896)
Camphoric acid Camphoric anhydride campholide
Homocamphoric acid Camphor
• Industrially camphor is obtained from α-pinine i.e.
from turpentine oil. Α-pinine Bornyl chloride
Camphene Isobornyl acetate Isoborneol Camphor.
• USES
• as plasticizer for celluloid & photographic film Mild
disinfectant & stimulant for heart muscle Used as
insect repellant Used as counter irritant As flavor
in soaps & cosmetics.
•Thank you

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STRUCTURE ELUCIDATION

Relation between general formula of compound and type of compounds:

General formula of parent saturated Hydrocarbon Type of structure

Molecular formula: molecular formula is determined by usual quantitative analysis

Camphor is a waxy, white or transparent

• α pinene Bornyl chloride Camphene

Isobornyl acetate Isoborneol Camphor

• The formation of these product shows that

• C10H16O + 2HN.NHC6H5 → C10H16=N-NH- C6H5

• Camphor on reaction with benzaldehyde gives

The formation of p-cymene reveals the presence of

• So by Knowing the structure of Camphoric acid

Aceto acetate Di methyl derivatives

• Glutaric acid Camphoric acid

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